Warren Berger: How Asking Questions Can Make You A Better Entrepreneur

I recently spoke to Warren Berger, who is the author of A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas. Berger has studied hundreds of the world’s leading innovators, entrepreneurs, and creative thinkers to learn how they ask questions, generate original ideas, and solve problems. His writing and research on questioning and innovation has appeared in Fast Company, Harvard Business Review, and Wired. His previous book, Glimmer, was an in-depth analysis of creative thinking that was named one of Business Week's “Best Innovation & Design Books of the Year.” In the following interview, Berger talks about how questioning can lead to new innovations, what the process of questioning is, why they fear the challenge of trying to get to the hard answers and shares his best advice to you.

Warren Berger

Dan Schawbel: How does questioning help entrepreneurs come up with their next great ideas?

Warren Berger: Questioning is often the starting point of innovation. I studied the origins of many breakthrough products and disruptive startup companies—and it’s amazing how often breakthroughs can be traced back to someone formulating (and then tackling) a question no one else was asking at the time. For example, Airbnb’s founders asking, Why are so many people unable to get a hotel room in San Francisco, while so many other people have an extra room in their home they’d love to make money off? What if we could connect these two needs?

The reality is, these kinds of opportunities are all around, but most people don’t notice them or take the next step, which is to inquire deeply about them. The successful entrepreneur is the one who “steps back” to question what others ignore or take for granted. Why does this situation or problem exist? What’s the opportunity here? How might I apply my own capabilities and imagination to take action on it?

Schawbel: What is the process of questioning and do you think you can take it too far?

Berger: As I learned from a research group called The Right Question Institute, questioning is a mental process that “enables us to organize our thoughts around what we don’t know.” And if we talk about innovative questioning—the kind I focus on in the book—to do that, we must marshal our intellectual resources to 1) understand a problem, 2) imagine and consider possible solutions, and 3) turn those ideas into reality. All of that tends to happen via questioning—typically starting with “Why” questions, then moving to “What if” idea-generating questions, and finally working through the “How” questions (as in, How do we actually get this done?).

Most innovation stories I studied went through some version of this inquiry progression. Not to suggest there is a formula for questioning—there isn’t—but there are stages in the innovation cycle when some types of questions work better than others. As to whether questioning can go too far? Yes—if you get trapped in those early stages of wide-open questioning, and you don’t keep moving ahead to more practical questions; i.e., if you’re stuck in “Why” and “What if,” and never get to “How.” To me questioning without action is not innovation—it’s philosophy. (Not that there’s anything wrong with philosophy!).

Schawbel: Why are entrepreneurs often reluctant to ask the right questions? Is it because they fear the right answers?

Berger: I don’t think they fear the answers, I think they fear the challenge of trying to get to the truly hard answers—and so they don’t ask the hard questions. Because if you dare to ask a big question, you are, in effect, issuing a challenge—to yourself or your company. And if you feel deep down you’re not up to that challenge, you’ll just avoid asking such questions. It’s much easier to ask more proscribed, practical questions—How can we move the sales needle by 2% this quarter—as opposed to asking, Why are we still doing things the way we’ve done it the past 20 years? How might we re-invent this process, this company, or this whole category?

Schawbel: Can you share an example of a CEO that has used questioning to their benefit and explain how?

Berger: One of the CEO’s featured in the book is Ron Shaich of Panera Bread, who uses questioning to keep moving the company forward and expanding its scope. Panera tackles questions like, What does the world need most… that we are uniquely able to provide? That “mission question” guides their new initiatives. Nike’s Mark Parker is another example of a great questioner: For years, he’s been asking, in effect, What is this company really about, beyond athletic apparel? What business are we really in? That has helped Nike become an active-lifestyle digital companion to its customers.

I also think Reed Hastings of Netflix is a great questioner; he started Netflix with a question (Why should I have to pay these Blockbuster late fees?) and he’s been questioning ever since, and in the process, continually expanding what Netflix does. And to this list I would add Jack Dorsey, whose credo is “Question everything,” and whose newest venture Square began with the question, Why can’t everyone accept credit cards?

Schawbel: What are your top pieces of career advice?

Berger: First, everyone says to “lean in” and “go for it”—but it’s also important to take time to “step back” and question. Why are you choosing that particular mountain to climb? Is it the best use of your strengths? What do you imagine awaits you at the top? What are you leaving behind, down below? How might you better enjoy the climb itself? Ask yourself a lot of questions—then go for it.

Second: Try to avoid becoming a “comfortable expert”—better to remain a “restless learner.” Nowadays, expertise tends to become outdated and obsolete. A questioner keeps adding to (or rethinking) what he/she “knows.” As Einstein said, “never lose a holy curiosity.”

Dan Schawbel is a workplace speaker and the New York Times best-selling author of Promote Yourself. Subscribe to his free monthly newsletter for more career tips.